It’s more common now than ever to experience—or choose—career shifts, even as a senior executive. Today, we’re diving deep with Jeff Epstein, Operating Partner at Bessemer Venture Partners and experienced CFO. Jeff and Matt discuss the ins and outs of career transitions and the surprises that come with them, from role changes to new industries to vastly different organizational structures. “I always wanted to develop a circle of competence and then over time expand the circle,” Jeff says. “You just learn more.” Another way to learn more and expand your career? Sitting on a board. The two discuss what it’s like to be a board member for different types of organizations, and even what it’s like to serve on the board of a company that fails. Tune in to follow Jeff’s career journey, hear about the lessons he learned firsthand, and get his advice for founders looking to scale.

We’re turning the tables with an Ask Bolster episode! Matt shares his playbook for building effective teams and developing leaders with a growth mentality. Nick Francis is the co-founder and CEO of Help Scout, a customer support platform for growing businesses. Today, he and Matt discuss what it takes to cultivate in-house talent and embody organizational values.

Fred Wilson has been a venture capitalist since 1987—so it’s fair to say he’s witnessed a few founders and become familiar with their most common mistakes. On today’s episode, he talks about the challenges facing founder teams, avoiding valuation misalignment, and finding the right deal.

Executives are often caught in the middle of the leadership dynamic, managing both up and down the organization. Establishing a framework or set of expectations for your working relationships can be a game-changer, but what exactly does that look like in practice? Cristina Miller is a seasoned, results-driven executive and board director with a strong track record in digital marketplaces, startups, and new business innovation. Today, she’s sharing what she’s learned about managing up.

If you’re leading an early-stage startup or a small business, chances are you interact regularly with everyone on your team. You have significant influence over the culture—but what happens when you’re one of many? What happens to company culture when you achieve your scaling goals?Nick Mehta is the CEO of Gainsight, where he has scaled the company from its founding team to over 1200 employees. Today, he’s sharing his top three tips to scale your culture as you scale your business.

Introducing The Daily Bolster—a quick-hitting podcast for startup leaders scaling their businesses. Every day, Matt Blumberg, Co-founder and CEO of Bolster, will be joined by experienced operators and industry experts who share their real-world experiences and practical advice. Follow Bolster or subscribe to make sure you don’t miss a thing. Have a question for Matt or one of our guests? Email us at thedailybolster@bolster.com.